Sodium hydride → 3-(Aminomethyl)benzoic acid hydrochloride

Temperature

80 °C

4.34 g (20.0 mmol) of di(t-butyl) iminodicarboxylate was added to a mixture of 800 mg (20.0 mmol) of sodium hydride (60% dispersion in mineral oil) and 50 ml of dimethylformamide. 1.71 g (10.0 mmol) of 3-chloromethylbenzoic acid was added to the obtained mixture, and they were stirred at 80° C. for 2 hours. After the concentration under reduced pressure, 40 ml of dioxane containing 4 M of hydrogen chloride was added to the residue, and they were stirred at room temperature overnight. A white precipitate thus formed was taken by the filtration and washed with ethyl acetate to obtain 3-aminomethylbenzoic acid hydrochloride as white crystals. A mixture of this aminomethyl compound, 10 ml of water, 10 ml of 28% aqueous ammonia and 3.00 g (71.4 mmol) of cyanamide was stirred at 60° C. for 7 days. The solvent was evaporated, and the residue was purified by the reversed-phase HPLC in the same manner as that in step 5 in Example 1 to obtain the title compound.

1. concentrationAfter the concentration under reduced pressure, 40 ml of dioxane containing 4 M of hydrogen chloride
2. additionwas added to the residue, and they
3. stirringwere stirred at room temperature overnight
4. customA white precipitate thus formed
5. filtrationwas taken by the filtration
6. washwashed with ethyl acetate

ORD record

ord-db7ee05540cf44fa9363b18f21aa4401

Source dataset

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06710056B2